RIMEGEPANT SULFATE ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C28H28F2N6O3.H2O4S
Molecular Weight	1167.193
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of RIMEGEPANT SULFATE ANHYDROUS

Structure Search

SMILES

OS(O)(=O)=O.N[C@H]1[C@@H](CC[C@@H](OC(=O)N2CCC(CC2)N3C(=O)NC4=C3C=CC=N4)C5=NC=CC=C15)C6=C(F)C(F)=CC=C6.N[C@H]7[C@@H](CC[C@@H](OC(=O)N8CCC(CC8)N9C(=O)NC%10=C9C=CC=N%10)C%11=NC=CC=C7%11)C%12=C(F)C(F)=CC=C%12

InChI

InChIKey=PQYZLKPVYCNNME-WLKALFMDSA-N

InChI=1S/2C28H28F2N6O3.H2O4S/c2*29-20-6-1-4-17(23(20)30)18-8-9-22(25-19(24(18)31)5-2-12-32-25)39-28(38)35-14-10-16(11-15-35)36-21-7-3-13-33-26(21)34-27(36)37;1-5(2,3)4/h2*1-7,12-13,16,18,22,24H,8-11,14-15,31H2,(H,33,34,37);(H2,1,2,3,4)/t2*18-,22+,24-;/m00./s1

HIDE SMILES / InChI

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C28H28F2N6O3
Molecular Weight	534.5571
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23965396

Bristol-Myers Squibb developed Rimegepant, also known as BMS-927711. Rimegepant is a potent, selective, competitive and orally active calcitonin gene-related peptide (CGRP) antagonist in clinical trials for treating migraine. Rimegepant has shown in vivo efficacy without vasoconstrictor effect; it is superior to placebo at several different doses (75 mg, 150 mg, and 300 mg) and has an excellent tolerability profile.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcitonin gene-related peptide type 1 receptor 9 Target ID: CHEMBL3798 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23153230	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute migraine 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965396	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1045.53 ng/mL OTHER https://www.biohavenpharma.com/sites/default/files/documents/rimegepant-ph1-elderly-pk-2019-ahs.pdf	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		RIMEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4718.71 ng × h/mL OTHER https://www.biohavenpharma.com/sites/default/files/documents/rimegepant-ph1-elderly-pk-2019-ahs.pdf	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		RIMEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.398 h OTHER https://www.biohavenpharma.com/sites/default/files/documents/rimegepant-ph1-elderly-pk-2019-ahs.pdf	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		RIMEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years Health Status: unhealthy Age Group: 18-75 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	Other AEs: Nausea, Hypersensitivity... Other AEs: Nausea (2%) Hypersensitivity (<1%) Dyspnea (<1%) Rash (grade 3, <1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
2250 mg single, oral Overdose Dose: 2250 mg Route: oral Route: single Dose: 2250 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	healthy, adults Health Status: healthy Age Group: adults Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf
75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	Other AEs: Nausea, Urinary tract infection... Other AEs: Nausea (1.8%) Urinary tract infection (1.5%) Transaminases increased (2.3%) Back pain (0.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	Other AEs: Nausea, Urinary tract infection... Other AEs: Nausea (2%) Urinary tract infection (1%) Dizziness (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/
600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf

AEs

AE	Significance	Dose	Population
Nausea	2%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years Health Status: unhealthy Age Group: 18-75 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Dyspnea	<1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years Health Status: unhealthy Age Group: 18-75 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Hypersensitivity	<1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years Health Status: unhealthy Age Group: 18-75 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Rash	grade 3, <1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years Health Status: unhealthy Age Group: 18-75 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Back pain	0.2%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Urinary tract infection	1.5%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Nausea	1.8%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Transaminases increased	2.3%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Dizziness	1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/
Urinary tract infection	1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/
Nausea	2%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults Health Status: unhealthy Age Group: adults Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	substrate 1193 inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C19 2057 UGT1A1 246 P-gp 1741 BCRP 910 OATP1B1 1079 OATP1B3 961 OAT1 725 OAT3 747 MATE2 267 MATE1 415 OCT2 779 L-type Ca channels 9	P-gp 2052 BCRP 697 OATP1B1 503 OATP1B3 435	CYP1A2 832 CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 6.04 uM]
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >10 uM]
MATE2 267	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >10 uM]
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >10 uM]
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >100 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
UGT1A1 303	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >50 uM]
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [Inhibition 5 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [Inhibition 5 uM]
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no
L-type Ca channels 9	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000PharmR.pdf#page=16 Page: 16.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	weak
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	yes [IC50 1.08 uM]
MATE1 416	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	yes [IC50 1.18 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	major	yes (co-administration study) Comment: In a dedicated drug interaction study, concomitant administration of 75 mg rimegepant (single dose) with itraconazole (200 mg once daily; at steady state) resulted in increased exposures of rimegepant (AUC by 4-fold & Cmax by ~1.5-fold). It is recommended to avoid concomitant administration of rimegepant with a strong inhibitor of CYP3A4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	minor	no (co-administration study) Comment: In a dedicated drug interaction study, concomitant administration of 75 mg rimegepant (single dose) with fluconazole (400 mg once daily; at steady state) resulted in increased exposures of rimegepant (AUC by 1.8-fold) with no relevant effect on Cmax. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=36 Page: 36.0	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=36 Page: 36.0	no
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000PharmR.pdf#page=16 Page: 16.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA009C73	https://www.aablocks.com/goods/Goods/detail?id=AA009C73
AbMole Bioscience	M9165	http://www.abmole.com/products/rimegepant.html
Achemtek	0102-014007	http://www.achemtek.com/1289023-67-1
Adooq BioScience	A13102	https://www.adooq.com/bms-927711.html
AK Scientific, Inc. (AKSCI)	3504AH	http://www.aksci.com/item_detail.php?cat=3504AH
Ambinter	Amb24059710	http://www.ambinter.com/reference/24059710
Aurum Pharmatech LLC	W-5991	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5991
BioCrick	BCC1433	http://www.biocrick.com/BMS-927711-BCC1433.html
Chem Scene	CS-1027	http://www.chemscene.com/1289023-67-1.html
Chemspace	CSSB00102527123	https://chem-space.com/CSSB00102527123
DC Chemicals	DC12800	http://www.dcchemicals.com/product_show-Rimegepant.html
eNovation Chemicals	D663125	https://www.enovationchem.com/ProductDetails.asp?ProductID=D663125
Excenen	EX-A1922	https://www.excenen.com/searchresultlist.php?id=1289023-67-1
Lab Network	LN01301576	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01301576
MedChem Express	HY-15498	https://www.medchemexpress.com/BMS-927711.html
MuseChem	I001123	https://www.musechem.com/product/I001123.html
Selleck Chemicals	S6659	http://www.selleckchem.com/products/bms-927711.html
Smolecule	S541433	http://www.smolecule.com/products/s541433
THE BioTek	bt-280698	https://www.thebiotek.com/product/inhibitors/bt-280698

PubMed

Title	Date	PubMed
Asymmetric Synthesis of Heterocyclic Analogues of a CGRP Receptor Antagonist for Treating Migraine.	2015-12-18	26650258

Patents

Sample Use Guides

In Vivo Use Guide

10 mg, 25 mg, 75 mg, 150 mg, 300 mg, 600 mg one per day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:29 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:29 GMT 2025`
Record UNII	687X3KJY2O
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

1-PIPERIDINECARBOXYLIC ACID, 4-(2,3-DIHYDRO-2-OXO-1H-IMIDAZO(4,5-B)PYRIDIN-1-YL)-, (5S,6S,9R)-5-AMINO-6-(2,3-DIFLUOROPHENYL)-6,7,8,9-TETRAHYDRO-5H-CYCLOHEPTA(B)PYRIDIN-9-YL ESTER, SULFATE (2:1)

Preferred Name

English

RIMEGEPANT SULFATE ANHYDROUS

Common Name

English

DI((5S,6S,9R)-5-AMINO-6-(2,3-DIFLUOROPHENYL)-6,7,8,9-TETRAHYDRO-5H-CYCLOHEPTA(B)PYRIDIN-9-YL 4-(2-OXO-2,3-DIHYDRO-1H-IMIDAZO(4,5-B)PYRIDIN-1-YL)PIPERIDINE-1-CARBOXYLATE), MONOSULFATE

Systematic Name

English

Code System Code Type Description

SMS_ID

300000023333

Created by admin on Mon Mar 31 18:03:29 GMT 2025 , Edited by admin on Mon Mar 31 18:03:29 GMT 2025

PRIMARY

FDA UNII

687X3KJY2O

Created by admin on Mon Mar 31 18:03:29 GMT 2025 , Edited by admin on Mon Mar 31 18:03:29 GMT 2025

PRIMARY

PUBCHEM

76972049

Created by admin on Mon Mar 31 18:03:29 GMT 2025 , Edited by admin on Mon Mar 31 18:03:29 GMT 2025

PRIMARY

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					1383NM3Q0H

RIMEGEPANT SULFATE

SOLVATE->ANHYDROUS

Related Record Type Details


					997WVV895X

RIMEGEPANT

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23965396

Originator

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23965396

C_max

T_1/2

Drug as perpetrator